This time last year Novak Djokovic’s march towards history had never been clearer; the Serb scored a third straight major victory of the season to tie Roger Federer and Rafael Nadal at 20 major titles apiece. Only the US Open stood between him from not only surpassing his Big 3 rivals, but also a Calendar Year Grand Slam that would definitively put him a cut above the rest.

We all know what happened since: the CYGS dream ended in a lackluster final that reduced Djokovic to tears on Arthur Ashe Stadium, and now it’s Nadal in a credible hunt for all four majors after winning the Australian Open and Roland Garros. Defying destiny in favor of an ill-advised stance, the former No. 1’s refusal to be vaccinated against COVID-19 has cost him both his spot atop the ATP rankings and a chance to compete in the tour’s two hard-court majors. Having already missed Melbourne under cataclysmic circumstances, the US Open will likely also be off-limits barring a policy change allowing foreigners to enter the U.S. without a vaccination.

None of that has mattered thus far at the All England Club, where Djokovic has largely looked back to his unbeatable best through four matches. Might he earn some overdue redemption with a seventh Wimbledon crown?

Here’s why—and why not—he’ll make it happen.


Why He’ll Win

If you need a hard sell on Djokovic at Wimbledon, you’ve probably been living under a rock for the last decade. The 35-year-old has won the last three Championships and five of the last seven, often scoring wins over Federer and Nadal in the process.

In his 2021 Wimbledon campaign, he dropped just two sets in seven matches and withstood a worthy challenge from big-serving Matteo Berrettini in the final. The Italian, who arrived to SW19 having won back-to-back title on grass, looked to be his biggest threat until he was felled by a COVID-19 diagnosis that forced him out of the tournament before he could even take the court.

Another pre-tournament contender, Hubert Hurkacz, bowed out in a dramatic first-rounder to Alejandro Davidovich Fokina, and as the draw comes down to eight remaining athletes, only Djokovic and Nadal have a previous major semifinal on their resume. No. 10 seed Jannik Sinner, who ousted Carlos Alcaraz in the fourth round, and the winner of David Goffin and No. 9 seed Cameron Norrie stand between Djokovic and an eighth Wimbledon final, where he boasts an incredible 6-1 record.

Though Nadal beat him in their most recent meeting at Roland Garros, Djokovic has been clearly trending up since stumbling through the early part of the clay-court swing, storming to victory at the Internazionali BNL d’Italia and looking near-perfect through the first week of Wimbledon.

Facing off on Djokovic’s best surface, the momentum surely favors the Serb in a final where Nadal aims to win “just” a third Wimbledon title and deal with the pressure of keeping his Calendar Year Grand Slam bid alive.

Smooth sailing, right?

I would like to be in the last match to eventually make history, of course, of this tournament that, as I said, as a seven-, eight-year-old boy I've dreamt of winning Wimbledon and becoming No. 1. That was always biggest motivation I had as a kid. Novak Djokovic on potentially winning a fourth straight Wimbledon title

Why He Won’t

The Calendar Year Grand Slam does funny things to players. Serena Williams was on her own quest for the mantle in 2015; by the time she sealed a second Non-Calendar Year “Serena” Slam at that year’s Championships, she had improved to 21-4 in major finals, and was a combined 44-7 once she reached the semis at a Slam.

Since enduring that earth-shattering loss to Roberta Vinci two wins from the CYSGS at the US Open, she is 2-6 in championship matches.

While Djokovic can cite rust in some of his clay-swing defeats, he was decidedly unclutch against Nadal under the Roland Garros lights: with a clear path to force a deciding set a 5-2 in the fourth, the top seed found himself outplayed by Nadal as he lost five of the next six games and tiebreaker, 7-4.

There’s not enough data to declare this a longterm issue, but it’s certainly troubling that he was unable to stay focused in such an important match and—with all eyes on Nadal’s questionable foot—an ostensibly hindered opponent.

He’ll have the benefit of tremendous experience in his next two matches, but he’ll also have one player feeling no pressure to score his major breakthrough (Sinner) and another with all of Great Britain behind him (Norrie). Having played so few big matches since his US Open disappointment, how quickly will he readjust to that kind of pressure?

This next week will either remind us who Novak Djokovic is, or introduce us to a new character entirely. Stay tuned to find out.